Strategic Programs Leader/Chief of Staff

POSITION SUMMARY

The Leader of Strategic Programs/COS drives internal organizational program and project management on behalf of the Executive Leadership Team (ELT), turning strategic priorities into coordinated, well-governed execution. This role acts as a force multiplier, enabling leaders to focus on high-priority decisions while ensuring that organizational initiatives are executed efficiently; monitors progress across cross-functional initiatives, keeps stakeholders accountable to deadlines, and removes roadblocks so leadership's strategic agenda moves forward on schedule. The ideal candidate is a creative problem solver with a strong bias toward operational effectiveness, is comfortable using project and work-management tools to bring visibility and structure to fast-moving initiatives and is seeking to build the breadth of experience needed to advance into a leadership role.

SPECIFIC JOB RESPONSIBILITIES

• Strategic Initiative & Program Management

  • Serve as the internal program/project management lead for organization-wide initiatives sponsored by the Executive Leadership Team.
  • Work collaboratively with Executive Leadership to translate strategic priorities into structured plans, workstreams, and measurable milestones.
  • Build and maintain a portfolio view of active initiatives, surfacing status, risks, and dependencies to leadership on a regular cadence.
  • Maintain a keen focus on meeting deadlines under pressure, adjusting plans proactively when priorities or timelines shift.
  • Acting as a liaison, they translate executive priorities to teams and communicate organizational updates back to leadership.
  • They may lead high-impact projects, prepare executives for key meetings, and respond to urgent organizational challenges.
  • Provide data‑backed insights, challenge assumptions, and support executive decision‑making.

  Stakeholder Accountability & Execution

  • Monitor progress against target goals and deadlines across departments, escalating issues before they threaten delivery.
  • Motivate and hold stakeholders accountable to commitments, using influence rather than direct authority to drive follow-through.
  • Facilitate working sessions and check-ins to keep cross-functional teams aligned and moving in the same direction.
  • Act as a creative problem solver, identifying practical paths forward when initiatives hit obstacles or competing priorities.

  Operational Effectiveness

  • Identify opportunities to improve internal processes, communication, and reporting so initiatives run more efficiently over time.
  • Establish and maintain reporting frameworks and dashboards that give leadership early visibility into risks and outcomes.
  • Standardize how initiatives are tracked and communicated across the organization, using project management tools.
  • Support Executive Leadership with ad hoc analysis, briefing materials, and follow-up needed to keep decisions moving.
  • Perform other duties within the scope of the role as assigned.

EXPERIENCE REQUIRED

• • 7+ years of experience in program/project management, consulting, business operations, or a similar cross-functional role.
  • Demonstrated experience working directly with senior or executive leadership to drive strategic initiatives to completion.
  • Track record of managing multiple concurrent initiatives, deadlines, and stakeholders in a fast-paced environment.

QUALIFICATIONS, SKILLS, & KNOWLEDGE

• • Bachelor's degree in Business Administration, Management, or a related field, or equivalent practical experience; Masters preferred.
  • Technically savvy, with proficiency in project/work-management platforms such as Asana or Monday.com, and the Microsoft Office Suite.
  • Strong organizational and time-management skills, with sound decision-making and good judgment under pressure.
  • Excellent written and verbal communication skills, with the ability to influence and motivate stakeholders at all levels.
  • Nimble business mind, focused on developing creative solutions; a resourceful problem solver who can find a path forward amid ambiguity or competing priorities.
  • Demonstrated interest in, and aptitude for, advancing toward broader operational leadership.
  • Proactive, creative, intuitive, and enjoys working within a high growth, results-driven organization.
  • Ability to embrace Clearwater’s CLEAR core values (Commitment to Client Success, Lead with Accountability, Integrity & Collaboration, Excellence in All That We Do, Advance Colleague Success, Respect & Transparency) and culture.

The base salary range for this role is $140,000-150,000. Base salary is part of our total rewards package which also includes the opportunity for merit-based salary increases, eligibility for our 401(k) plan, medical, dental, vision, life and disability insurances and leaves provided in line with your work state. Our robust time-off policy includes flexible paid time off, 11 paid holidays, and paid sick time. Total compensation, including base salary to be offered, will depend on elements unique to each candidate, including applicable candidate experience, skills, education and other factors permitted by law.

Disclaimer: The above statements are intended to describe the general nature and level of work being performed by people assigned to this position. They are not to be construed as an exhaustive list of all responsibilities, duties, and skills required of colleagues in the role. All colleagues may be required to perform duties outside of their normal responsibilities from time to time, as needed.

Clearwater is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. Please inform Clearwater/Redspin’s Recruiting team if you need any assistance completing any forms or to otherwise participating in the application process.

Mental/Physical Requirements: Fast paced environment handling multiple demands. Must be able to exercise appropriate judgment as necessary. Requires a high level of initiative and independence. Excellent written and oral communication skills required. Requires the ability to use a personal computer for extended periods of time.

Disclaimer: The above statements are intended to describe the general nature and level of work being performed by people assigned to this position. They are not to be construed as an exhaustive list of all responsibilities, duties, and skills required of colleagues in the role. All colleagues may be required to perform duties outside of their normal responsibilities from time to time, as needed.

Clearwater is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. Please inform Clearwater/Redspin’s Recruiting team if you need any assistance completing any forms or to otherwise participating in the application process.

Mental/Physical Requirements: Fast paced environment handling multiple demands. Must be able to exercise appropriate judgment as necessary. Requires a high level of initiative and independence. Excellent written and oral communication skills required. Requires the ability to use a personal computer for extended periods of time.